Ethyl bromoacetate → {3-[3-(Quinolin-2-ylmethoxy)-benzyl]-indol-1-yl}-acetic acid

HRID 892213Notes

Reaction equation

HRID 892213 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=2)[O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:4]1.Br[CH2:32][C:33]([O:35]CC)=[O:34]>CN(C=O)C>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[CH2:17][O:16][C:15]1[CH:14]=[C:13]([CH:30]=[CH:29][CH:28]=1)[CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:3]([CH2:32][C:33]([OH:35])=[O:34])[CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 222415112-[3-(1H-Indol-3-ylmethyl)-phenoxymethyl]-quinoline

Product 1

HCID 22241553{3-[3-(Quinolin-2-ylmethoxy)-benzyl]-indol-1-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 22 mg, 0.55 mmol) is added to a solution of 2-[3-(1H-indol-3-ylmethyl)-phenoxymethyl]-quinoline (90 mg, 0.25 mmol, example 90) in DMF (2.5 mL). After stirring 5 minutes ethyl bromoacetate (0.1 mL, 0.9 mmol) is added and the reaction is allowed to stir 2 h. The reaction is partitioned between ethyl acetate and ammonium chloride and the organic phase is washed with water. The organic phase is dried over magnesium sulfate, concentrated and then the solid is titurated with ethyl ether and ethyl acetate to provide the title compound as a solid. m.p. 151–159° C.; 1H NMR (300 MHz, CDCl3) δ 8.20 (t, 2H), 7.83–7.80 (m, 1H), 7.77–7.71 (m, 1H), 7.67 (d, 1H), 7.61–7.53 (m, 1H), 7.45–7.42 (m, 1H), 7.29–7.14 (m, 3H), 7.05–6.99 (m, 2H), 6.94 (s, 1H), 6.85 (m, 2H), 5.16 (s, 2H), 4.84(s, 2H), 4.11 (s, 2H); MS (ESI) 423 (M+H)+.

Workup

  1. additionis added
  2. customThe reaction is partitioned between ethyl acetate and ammonium chloride
  3. washthe organic phase is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34de95c285ca4640bd6a7858a7e76018
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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